title: Development of glycosylation using the glucopyranose 1,2-orthobenzoate under electrochemical conditions.
abstract: Substituted glucopyranose 1,2-orthobenzoate undergoes β-selective glycosylation. The developed orthobenzoate derivative was stable under standard workup conditions and efficiently provided a variety of glycosides by EGA (electrogenerated acid), produced by anodic oxidation of cyclohexanol. Upon comparison with Lewis and Brønsted acids, EGA superiorly affected activation of the orthoester to afford desired glycosides possessing such aglycons as sugars, steroids, and adamantanes.
authors.affiliation: Department of Chemistry, Faculty of Science and Technology, Keio University , Hiyoshi 3-14-1, Kohoku-ku, Yokohama 223-8522, Japan.
authors.forename: Kohei
authors.initials: K
authors.lastname: Kawa
authors.forename: Tsuyoshi
authors.initials: T
authors.lastname: Saitoh
authors.forename: Eisuke
authors.initials: E
authors.lastname: Kaji
authors.forename: Shigeru
authors.initials: S
authors.lastname: Nishiyama
mesh_terms: D001565:Benzoates / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry*; D006031:Glycosylation; D015394:Molecular Structure; D009005:Monosaccharides / Q000737:chemistry*; D010084:Oxidation-Reduction
chemical_list: D001565:Benzoates; D006027:Glycosides; D009005:Monosaccharides